Paddle Annapolis: Kayaking & Paddle Boarding on Maryland’s Waters

Annapolis, Maryland, holds a unique place on the map as a vibrant sailing hub cradled by Chesapeake Bay’s extensive waterways. Paddle Annapolis is a standout outfitter in this historic seaport city, offering accessible paddle boarding and sit-on-top kayak experiences that capture the waterborne spirit of the area. From the calm inner harbor to the bay’s fringes, the mix of freshwater and brackish marshlands, dotted with ducks, herons, and the occasional osprey, makes for a rewarding trip on the water.

At Paddle Annapolis, guests can book a variety of rentals and guided tours tailored to all comfort levels, from solo sit-on-top kayaks to tandem kayaks perfect for partners or families. Paddle board rentals and guided paddle board tours provide a fresh vantage point over Annapolis’s waterways. The company prides itself on quick, friendly service — whether you walk up or reserve ahead — and a local team that shares a grounded knowledge of harbor routes, safety, and nearby points of interest.

Guided tours typically last around two hours, offering a blend of relaxed paddling and storytelling. Guides bring Annapolis's maritime history and natural highlights to life, revealing quieter coves and scenic views of the docks where classic sailboats line up. Kayaks and paddle boards launch easily from Yacht Haven Marina, where parking is convenient but limited, underscoring the need for early arrival during busy summer weekends.

What sets Paddle Annapolis apart is its approachable location in a bustling city known for boating, yet it maintains a calm, inclusive atmosphere ideal for families, couples, and solo adventurers. Bringing a dog along is welcomed, making the experience even more personal. Whether embarking on a tranquil morning paddle or a breezy afternoon tour, Paddle Annapolis offers an authentic connection to Chesapeake Bay’s water culture and natural charm right from the heart of Maryland’s capital city.